So, Let's try to get things in order:
Do you need anything beyond the base kit for the raspberry pi mounting?
Yes, You want 4X of
the board standoffs, and IIRC, you may need to buy or get a small amount of wire for wiring it up. Nothing major.
Can you send G-code from S3D to astro/octoprint or any other print host?
Yes. G-code is G-code. If it will run on a standard machine, it should be uploadable to web-based print hosts.
Are there advantages to the Duet Wifi:
Most definitely. Advantage one, higher micro-stepping capacity and amperage limits, meaning you could increase power and resolution with the right motors (at the highest microstepping levels, you will lose substaintial torque, and likely would need to increase the amperage a lot, and then need to bump up the voltage to get the speed back, but it is possible). No segmentation artifacts and a much cleaner, denser calibration capability, with no need for anything other than the built in leveling macros, meaning no fiddling with plugins or web pages. Additionally, it has a nicer PID tuning model, and supports keeping models on the board itself, or using a removable SD card to bring files to the machine. Beyond that, it's also got support for PT100 and thermocouple temperature sensors, which are both more accurate.
Do FSR's have any advantages for you?
If you're using the Duet WIFI, definitely, as they enable probing for it, and other 3rd party boards or firmware builds. A lot of us prefer them as well because they are connected to the bed, and don't need to be matched one to one with the hotend. You can also swap bed surfaces with less work, as the accelorometer doesn't like Fablam, Buildtak, or PEI very much. It's also less likely to deform the nozzle or chip the glass than ramming at a high speed would.
Now, I can give you opinions on other upgrades, but that handles the questions, I think.